Journal of Organic Chemistry, volume 80, issue 24, pages 12212-12223
Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly
Ekaterina M Budynina
1, 2
,
Olga Ivanova
1, 2
,
Alexey O Chagarovskiy
1, 2
,
Yuri Grishin
1
,
Igor V Trushkov
1, 2
,
Publication type: Journal Article
Publication date: 2015-12-01
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
We report a new simple method to access highly substituted cyclopentanes via Lewis acid-initiated formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes to 1,3-dienes. This process displays exceptional chemo- and regioselectivity as well as high diastereoselectivity, allowing for the synthesis of functionalized cyclopentanes and bicyclic cyclopentane-based structures in moderate to high yields. Moreover, one-pot synthesis of biologically relevant cyclopentafuranones, based on reaction of donor-acceptor cyclopropanes with dienes, has been developed.
Top-30
Citations by journals
|
1
2
3
4
5
|
|
|
Organic and Biomolecular Chemistry
5 publications, 17.86%
|
|
|
European Journal of Organic Chemistry
4 publications, 14.29%
|
|
|
Journal of Organic Chemistry
3 publications, 10.71%
|
|
|
Tetrahedron
2 publications, 7.14%
|
|
|
Tetrahedron Letters
2 publications, 7.14%
|
|
|
Advanced Synthesis and Catalysis
2 publications, 7.14%
|
|
|
Chem Catalysis
1 publication, 3.57%
|
|
|
ChemInform
1 publication, 3.57%
|
|
|
Chemistry - A European Journal
1 publication, 3.57%
|
|
|
ChemistrySelect
1 publication, 3.57%
|
|
|
Chemical Record
1 publication, 3.57%
|
|
|
Angewandte Chemie - International Edition
1 publication, 3.57%
|
|
|
Angewandte Chemie
1 publication, 3.57%
|
|
|
Organic Reaction Mechanisms
1 publication, 3.57%
|
|
|
Synlett
1 publication, 3.57%
|
|
|
Russian Chemical Reviews
1 publication, 3.57%
|
|
|
1
2
3
4
5
|
Citations by publishers
|
2
4
6
8
10
12
14
|
|
|
Wiley
13 publications, 46.43%
|
|
|
Elsevier
5 publications, 17.86%
|
|
|
Royal Society of Chemistry (RSC)
5 publications, 17.86%
|
|
|
American Chemical Society (ACS)
3 publications, 10.71%
|
|
|
Thieme
1 publication, 3.57%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 3.57%
|
|
|
2
4
6
8
10
12
14
|
- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0,0,0,0],"codes":[0,0,0,0,0,0,0,0,0],"imageUrls":["","","","","","","","",""],"datasets":[{"label":"Citations number","data":[7,5,0,4,1,6,2,1,2],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["25","17.86",0,"14.29","3.57","21.43","7.14","3.57","7.14"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Organic and Biomolecular Chemistry","European Journal of Organic Chemistry","Journal of Organic Chemistry","Tetrahedron","Tetrahedron Letters","Advanced Synthesis and Catalysis","Chem Catalysis","ChemInform","Chemistry - A European Journal","ChemistrySelect","Chemical Record","Angewandte Chemie - International Edition","Angewandte Chemie","Organic Reaction Mechanisms","Synlett","Russian Chemical Reviews"],"ids":[541,19472,8697,3439,6133,3906,26939,25372,24708,8021,22413,19215,25450,42256,10217,23802],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[5,4,3,2,2,2,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[17.86,14.29,10.71,7.14,7.14,7.14,3.57,3.57,3.57,3.57,3.57,3.57,3.57,3.57,3.57,3.57],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Wiley","Elsevier","Royal Society of Chemistry (RSC)","American Chemical Society (ACS)","Thieme","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[11,17,123,40,135,9422],"codes":[0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[13,5,5,3,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[46.43,17.86,17.86,10.71,3.57,3.57],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartiles":{"type":"bar","data":{"show":true,"labels":[2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[1,0,0,0,1,0,0,0,0],"percentage":["3.57","0","0","0","3.57","0","0","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[2,3,0,0,0,1,0,1,1],"percentage":["7.14","10.71","0","0","0","3.57","0","3.57","3.57"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[3,2,0,3,0,5,2,0,1],"percentage":["10.71","7.14","0","10.71","0","17.86","7.14","0","3.57"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,0,0,1,0,0,0,0,0],"percentage":["3.57","0","0","3.57","0","0","0","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by SCImago per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartilesWs":{"type":"bar","data":{"show":true,"labels":[2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[2,2,0,0,1,0,0,1,0],"percentage":["7.14","7.14","0","0","3.57","0","0","3.57","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[2,1,0,2,0,3,1,0,1],"percentage":["7.14","3.57","0","7.14","0","10.71","3.57","0","3.57"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[2,2,0,1,0,2,0,0,1],"percentage":["7.14","7.14","0","3.57","0","7.14","0","0","3.57"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,0,0,1,0,1,1,0,0],"percentage":["3.57","0","0","3.57","0","3.57","3.57","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by WoS per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Budynina E. M. et al. Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly // Journal of Organic Chemistry. 2015. Vol. 80. No. 24. pp. 12212-12223.
GOST all authors (up to 50)
Copy
Budynina E. M., Ivanova O., Chagarovskiy A. O., Grishin Y., Trushkov I. V., Melnikov M. Y. Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly // Journal of Organic Chemistry. 2015. Vol. 80. No. 24. pp. 12212-12223.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.5b02146
UR - https://doi.org/10.1021/acs.joc.5b02146
TI - Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly
T2 - Journal of Organic Chemistry
AU - Chagarovskiy, Alexey O
AU - Budynina, Ekaterina M
AU - Ivanova, Olga
AU - Grishin, Yuri
AU - Trushkov, Igor V
AU - Melnikov, Mikhail Y.
PY - 2015
DA - 2015/12/01 00:00:00
PB - American Chemical Society (ACS)
SP - 12212-12223
IS - 24
VL - 80
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex
Copy
@article{2015_Budynina,
author = {Alexey O Chagarovskiy and Ekaterina M Budynina and Olga Ivanova and Yuri Grishin and Igor V Trushkov and Mikhail Y. Melnikov},
title = {Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly},
journal = {Journal of Organic Chemistry},
year = {2015},
volume = {80},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.joc.5b02146},
number = {24},
pages = {12212--12223},
doi = {10.1021/acs.joc.5b02146}
}
Cite this
MLA
Copy
Budynina, Ekaterina M., et al. “Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly.” Journal of Organic Chemistry, vol. 80, no. 24, Dec. 2015, pp. 12212-12223. https://doi.org/10.1021/acs.joc.5b02146.